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An Oxidopyrylium Cyclization/Ring-Opening Route to Polysubstituted α‑Hydroxytropolones

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journal contribution
posted on 2012-12-07, 00:00 authored by Christine Meck, Noushad Mohd, Ryan P. Murelli
α-Hydroxytropolones are a class of molecules with therapeutic potential against several human diseases. However, structure–activity relationship studies on these molecules have been limited due to a scarcity of efficient synthetic methods to access them. It is demonstrated herein that α-hydroxytropolones can be generated through a BCl3-mediated ring-opening/aromatization/demethylation process on 8-oxabicyclo[3.2.1]octenes. Used in conjunction with an improved method based on established oxidopyrylium dipolar cycloadditions, several polysubstituted α-hydroxytropolones can be accessed in three steps from readily available α-hydroxy-γ-pyrones.